Diketopyrrolo-pyrrole compounds

Abstract

A diketopyrrolo-pyrrole compound according to Formula (I): wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, a halogen atom, a methyl group, an ethyl group, an tert.-butyl group, a phenyl group, a cyano group, and an acid group; R 4 —, R 5 , and R 6 are independently selected from the group consisting of hydrogen, a halogen atom, a methyl group, an ethyl group, an tert.-butyl group, a phenyl group, and a cyano group; and wherein one of R 7 and R 8 is a group including two acid functions while the other one of R 7 and R 8 represents hydrogen. Pigment dispersions, methods for forming pigment dispersions, and use of the diketopyrrolo-pyrrole compound may include Formula (I).

1. A diketopyrrolo-pyrrole compound according to Formula (I): 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , and R 3  are independently selected from the group consisting of hydrogen, a halogen atom, a methyl group, an ethyl group, an tert.-butyl group, a phenyl group, a cyano group, and an acid group; 
         R 4 , R 5 , and R 6  are independently selected from the group consisting of hydrogen, a halogen atom, a methyl group, an ethyl group, an tert.-butyl group, a phenyl group, and a cyano group; and 
         one of R 7  and R 8  is a group including two acid functions while the other one of R 7  and R 8  represents hydrogen. 
       
     
     
       2. The diketopyrrolo-pyrrole compound according to  claim 1 , wherein the acid group for R 1 , R 2  and/or R 3  is a carboxyl group. 
     
     
       3. The diketopyrrolo-pyrrole compound according to  claim 2 , wherein R 1  and R 3  represent a carboxyl group, and R 2  represents hydrogen. 
     
     
       4. The diketopyrrolo-pyrrole compound according to  claim 1 , wherein R 1 , R 2 , and R 3  are independently selected from the group consisting of hydrogen, a halogen atom, a methyl group, an ethyl group, an tert.-butyl group, a phenyl group, and a cyano group. 
     
     
       5. The diketopyrrolo-pyrrole compound according to  claim 4 , wherein R 1 , R 3 , R 4 , and R 6  represent hydrogen. 
     
     
       6. The diketopyrrolo-pyrrole compound according to  claim 5 , wherein R 2  and R 5  represent a chloro atom. 
     
     
       7. The diketopyrrolo-pyrrole compound according to  claim 5 , wherein R 2  and R 5  represent hydrogen. 
     
     
       8. The diketopyrrolo-pyrrole compound according to  claim 5 , wherein R 2  and R 5  represent a phenyl group. 
     
     
       9. The diketopyrrolo-pyrrole compound according to  claim 1 , wherein the group including two acid functions R 7  or R 8  is selected from the group consisting of an alkanoic acid group, an alicyclic acid group, a heterocyclic acid group, a heteroaromatic acid group, and an aromatic acid group. 
     
     
       10. The diketopyrrolo-pyrrole compound according to  claim 9 , wherein the aromatic acid group is a phtalic acid group, an isophtalic acid group, or a terephtalic acid group. 
     
     
       11. A non-aqueous pigment dispersion comprising:
 the diketopyrrolo-pyrrole compound as defined by  claim 1 . 
 
     
     
       12. The non-aqueous pigment dispersion according to  claim 11 , wherein the pigment is selected from the group consisting of C.I. Pigment Orange 71, C.I. Pigment Orange 73, C.I. Pigment Orange 81, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, C.I. Pigment Red 270, C.I. Pigment Red 272, and mixed crystals thereof. 
     
     
       13. The non-aqueous pigment dispersion according to  claim 11 , wherein the pigment dispersion is a curable inkjet ink. 
     
     
       14. A method for forming a pigment dispersion comprising the steps of:
 (a) providing a diketopyrrolo-pyrrole compound according to  claim 1 ; 
 (b) transforming at least one of the two acid functions of the group including two acid functions R 7  or R 8  of the diketopyrrolo-pyrrole compound into a salt group; and 
 (c) mixing the diketopyrrolo-pyrrole compound with a pigment in a dispersion medium. 
 
     
     
       15. The method according to  claim 14 , wherein the salt group of R 7  or R 8  is an ammonium acid salt group. 
     
     
       16. The method according to  claim 15 , wherein the ammonium acid salt group is a substituted ammonium group selected from the group consisting of  + N(CH 3 ) 2 (C 18 H 37 ) 2 ,  + NH(CH 3 ) 2 (C 18 H 37 ),  + N(CH 3 ) 2 (C 12 H 25 ) 2 ,  + NH(CH 3 ) 2 (C 12 H 25 ),  + N(CH 3 ) 2 (C 10 H 21 ) 2 ,  + NH(CH 3 ) 2 (C 10 H 21 ),  + N(CH 3 ) 2 (C 8 H 17 ) 2 ,  + NH(CH 3 ) 2 (C 8 H 17 ),  + NH(C 8 H 17 ) 3 ,  + NH(C 10 H 21 ) 3 ,  + NH(C 12 H 25 ) 3 , and  + NH(C 18 H 35 ) 3 . 
     
     
       17. The method according to  claim 14 , wherein the pigment is selected from the group consisting of C.I. Pigment Orange 71, C.I. Pigment Orange 73, C.I. Pigment Orange 81, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264, C.I. Pigment Red 270, C.I. Pigment Red 272, and mixed crystals thereof. 
     
     
       18. The method according to  claim 17 , wherein the pigment dispersion is a curable inkjet ink. 
     
     
       19. A coated layer comprising the diketopyrrolo-pyrrole compound as defined in  claim 1 .